Sulphanilylaminohydantoin



Patented Sept. 18,1945 l 23 954 a w onrnmom George W. Ralziss, Le Roy W. Clemence; and Morris Freifelder, Philadelphia, Pa., assignors to Abbott Laboratories, a corporation of Ellinois No Drawing. Application April 7, 19%, Serial No. 387,260

3 Qlaims. (Cl. 260-23911) The present invention relates to chemical compositions and in particular to sulphanilamide de- O rivatives of 5-membered heterocyclic rings con- ("311 l; taining 2 nitrogen (Nlatoms. The compositions of the present invention are characterized by ther- 5 apeutic properties which make them valuable It w be understood that the Present invenagents for use in the pharmaceutical art. t is not l mit d to t e above e p In The following examples will serve to illustrate place of the a tam n -s lp ny cht present invention. a ride employed. for example, other acyl-amino- 1'0 benzene-sulphonyl halides may be used to couple Example I 5"sulfamlylammo'hydantmn with the amln' o-5-membered heterocyclic rings.

About 3 grams of 5-amino-hydantoin hydro- In such case the final amino products may be obchloride are suspended in aboutr1.5 cc. of pyridine tained by subjecting the acyl intermediate to a and to this mixture is gradually added about 4.7 hydrolyzing reaction or deacylation treatment in grams of p-acetamino-benzene-sulphonyl chloaccordance withstandard practices.

ride. The reaction mixture is warmed on a steam It will be understood that the process of prepabath or about 1.2 hours and the gummy mass obration may be modified by those skilled in the art tallied preferably allowed to stand over night. and that the scope of the present invention is About cc. of water is next added and the reto be interpreted in the light of the claims apsulting clear solution evaporated in vacuo. The 20 pended hereto.

gummy. solid obtained is hydrolyzed by refluxing We claim:

with 50 cc. of 5 per cent sodium hydroxide for I l. The compound 'sulfanilylaminohydantoin about 1.5 hours and the solution then allowed to having the formula evaporate spontaneously to a. thick mass. This mass is next filtered, the solid extracted with 100 O cc. of boiling absolute alcohol with heating under 00 reflux for several hours, and the insoluble material filtered off. The filtrate is then evaporated to dryness and the final product obtained may be Said commund being Prepared for use as a rf 11 in 1 so apelitlcrepresented by the 9 ow g formu 2. Compounds having the following linkage:

l NHOSOIN-HZH-IIJJIH i 5 v o o x NSlN'-CHNH N i l i! do do E'm'mple II-4-sulfdnilylamin0-pura2ole B About 2.4 grams of N-acetyl sulfanllyl chloride inlwmch x is a member of the g-mup consisting are added to about 1.56 grams of 4-amino-pyrar n and ac 1 an Yi i re d zole dihydrochloride dispersed in about 5 cc. of 40 gi s; g i g d s a cat p t pyridine and the reaction mixture warmed for about 1 hour at 60 C. Ice and water are next 9? the tollplowmg formula added along with about 5 cc. of concentrated hy- Q drochloric acid and the clear solution formed all lowed'to stand, 'e. 3. over night. The reaction Q mixture is then filtered and washed with cold H water, and the intermediate acetyl product lLv- Y 4 drolyzed by refluxing for about one hour with 15 in which Ac is an acyl group and Y is a cation, cc. of N/1 NaOH in the usual manner. The hyprepared for useas therapeutics.

. drolyzed' mixture is then cooled, neutralized with acid (H01), cooled and filtered. The final prodvGEORGE W. RAIZISS. uct recrystallized from about 10 cc. of hot water LE ROY W. CLEMENCE.

may be represented by the following formula. I MORRIS FREIFEIDER. 

